Tetrahydrofuran → (5,6-Dimethylpyridin-2-yl)methanol

HRID 1720359Notes

Reaction equation

HRID 1720359 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:15]1[CH:20]=[CH:19]C=C[N:16]=1)(OC)=O.[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH3:19][C:20]1[CH:23]=[CH:22][C:21]([CH2:25][OH:24])=[N:16][C:15]=1[CH3:11]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 755692-CarbomethoxypyridineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18413912(5,6-Dimethylpyridin-2-yl)methanol

Procedure

Diisobutyl aluminum hydride (4.45 mL, 25 mmol) was added to the carbomethoxypyridine from Step 3 (1.4 g, 8.4 mmol ) in THF (40 mL) at -78° C. The mixture was stirred overnight with slow warming to +4° C. The reaction was quenched with solid tartaric acid followed by aqueous sodium potassium tartrate and stirred 1/2 hour. Neutralization with saturated aq. NaHCO3 and extraction with EtOAc (3×) gave after treatment with brine and evaporation 1.12 g (97%) of the title compound.

Workup

  1. temperaturewith slow warming to +4° C
  2. customThe reaction was quenched with solid tartaric acid
  3. stirringstirred 1/2 hour
  4. extractionNeutralization with saturated aq. NaHCO3 and extraction with EtOAc (3×)
  5. customgave after treatment
  6. customwith brine and evaporation 1.12 g (97%) of the title compound

Sources & evidence

ORD record
ord-6407db1cdd284b9989495177c5cda325
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

Loading…